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Nature Chemistry

Thursday, January 12, 2012

Copper-catalyzed direct oxidative synthesis of α-ketoamides from aryl methyl ketones, amines, and molecular oxygen


The author report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford β-hydroxy aryl ketones in 73–94% yields as single regioisomers. The reactivity and regioselectivity were promoted by catalytic amounts of a phosphinite that forms a dynamic covalent bond with the allylic alcohol. Hydroacylation of 1,2- and 1,1-disubstituted olefins generates β-hydroxy aryl ketones bearing tertiary and quaternary centers, respectively.



Graphical abstract: β-hydroxy ketones prepared by regioselective hydroacylation

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